How professional gambler Mike Maloney keeps beating the odds in horse racing

LEXINGTON, Ky. – He has called Mike Maloney the Michael Jordan of horseplayers, and Sam Bowie would know.

The former University of Kentucky basketball star, famously drafted ahead of Air Jordan, has known Maloney for years through his own interest in horseplaying. Bowie has seen the process, the attention to detail, the different colored pens, the piles of information and notes, and the results.

“In life, some people are blessed at certain professions,” Bowie said of Maloney, “and no matter how hard you and I work at that same profession, they’ve got that gift, that ‘it’ factor. We say in sports, ‘He’s got it.’ Well, what is it? I don’t know what it is or how to describe it, but I know it when I see it.

“And he’s got it.”

Though there isn’t a way to track such things, it could be argued that Maloney, who risks millions in his work, has been the most consistently successful individual professional horseplayer anywhere.

His job is undoubtedly rare, largely solitary, occasionally lucrative, other times costly and endlessly demanding, meant only for a self-described workaholic who basically has to be that in order to keep winning enough to do it — which Maloney has now for almost 20 years.

Lexington's Mike Maloney has been among the best full-time professional horseplayers for almost two decades.(Photo: Scott Utterback/Courier Journal )

Beginning around 7 a.m. on a recent Saturday, Maloney had already spent a couple of hours prepping for a day of races when he arrived at his office in Lexington’s Red Mile harness track and simulcasting facility. Relatively inconspicuous in attire, mild-mannered in disposition and businesslike in demeanor, Maloney resembles perhaps a college professor instead of one of the most accomplished gamblers in horse racing.

He’s given a large, windowless office in which to work. It has a refrigerator, his own wagering machine and a large desk with notes and racing forms seated in front of a wall with 11 televisions that will be turned to active racetracks. He’ll plan each day to seriously play two or three of them while keeping an eye on opportunities elsewhere.

He might be there past 7 p.m., and he’ll get up the next day to do the same, studying races before and after they run, trying endlessly to beat a game with odds stacked against him, one that many would say is ultimately unbeatable. He works to prove otherwise.

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A Richmond native who lives in Lexington, the 63-year-old Maloney has been studying horse racing since age 15. But he turned pro, so to speak, about 20 years ago, becoming a full-time horseplayer and leaving his business as a wholesale antiques dealer.

“I was in my 30s before I ever began to consistently show a profit at the track,” Maloney said. “Then once that began to happen, I thought, ‘There’s a possibility here.’ … I haven’t had a negative year, but there are a lot of years where I’m not happy and I want to do better. Then there are some years that were really good. But it’s not a smooth ride. You know, it’s gambling, and you have to embrace it that way.”

Some may instinctively recoil. Others might believe he’s got the best job in the world.

But neither response does justice to how rare it is that Maloney has had the makeup to thrive full time in a profession that a select few could do — or would want to — with numbers that seemingly dwindle each year as the game grows more difficult.

“These days, the people betting the most money, it’s AI, it’s computers, it’s algorithms, stuff like that,” Fornatale said. “But for an individual, you can’t really name (anyone better). Other people I know who’ve been doing it for a comparable amount of time as Mike are, I think, more consciously phasing out as the market gets more efficient and the game gets tougher. He’s still there grinding away, and it’s the only job he’s had in nearly 20 years.

“He really is at the pinnacle. As far as I’m concerned, put him on the Mount Rushmore of horseplayers.”

Check out: At Panama's famed jockey school, aspiring riders dream to race in the Kentucky DerbyAs Bowie noted, “That’s not luck.” Maloney isn’t throwing darts at a board. Far from it, he’s chronicling the story of countless horses on a race-by-race basis at various tracks, ones he likes, others he doesn’t. In risking high amounts, he doesn’t trust tips or gut hunches. He strives to take instructions from numbers on paper, proprietary information he researches and assembles to handicap races.

“I’m almost a robot making the decisions and doing everything from a logical perspective,” Maloney said. “… The guys that choose to do this for a living, most of them don’t last very long. There are a lot of failed professional gamblers that go back to the real world. What takes most of them down is not that they are not good handicappers. When times are good they’re killing it, but when they run into the first real downdraft … they can’t withstand that. A big part of it is controlling your ego.”

What he has lost, Maloney said, is the fun of going to the racetrack with friends. It’s not that he intended that to happen. It’s just part of a pursuit that can threaten to take over your life.

Still to this day, by nature of what he does, his tends to be a solitary world. His success is built so much on developing his own information that he basically can’t take an extended vacation, because a slump will usually follow if he’s not paying attention. After all, these computer wagering syndicates he’s competing against “don’t make mistakes,” Maloney said.

And for someone operating “on 1 or 2% margin,” adjusting quickly is essential. Maloney doesn’t set winning goals. He instead sets limits to how much he is willing to lose. Then as he wins more, he allows himself to bet more. Losses mean he must make himself wager less, a test in self-control.

“When you leave the track and you’ve lost enough to buy a nice car, it gets your attention,” he said. “That’s part of the trade-off. I call it the emotional roller coaster. … And that doesn’t happen anymore. I’ve shrunk to where that’s not part of the equation. But at one time, it was. But you can also win a nice house.”

Maloney has remarried and is helping raise stepchildren, juggling soccer games with a demanding job.

He and his first wife divorced after about 20 years, and Maloney said in his book — one chapter he wrote himself was devoted to the personal aspects of his profession — that gambling played a part.

“I was really proud of that chapter,” said Maloney. “… The main things that I hit on are just honesty and communication and compromise. I think those are the key things (in a relationship).”

Asked his advice for those starting out as horseplayers, “No. 1, don’t quit your job,” Maloney replied with a laugh. “No. 2, be honest with yourself and approach gambling with caution.”

Maloney doesn’t bet as much as he did in past years, noting in his book that the amount he bet dipped from around $12 million in 2007 to around $4 million in 2016. These days, “It’s more than a million, but it’s way off of what I bet (in 2007),” Maloney said.

The reason for the drop has been the changing horse-racing industry. And that is a major concern for Maloney, who fears a dicey future for horse racing in a landscape where tracks’ takeouts on bets have increased as widespread competition looks to be coming from legalized sports betting.

“Racing is not geared up for this,” Maloney said. “… We are overpriced versus other forms of gambling, and now we’re going to face the biggest increase in competition that we have ever faced.”

Success — and especially finances — isn’t something Maloney is eager to discuss or publicize. People tend to get the wrong idea, he has learned.

Bodexpress acted up at times while galloping during Thursday morning workouts at Churchill Downs. He'll break out of post position 20 after the Wednesday scratch of Derby favorite Omaha Beach. May 2, 2019 Matt Stone/Courier Journal

Richard Mandella, trainer of Kentucky Derby hopeful Omaha Beach, talks to the media following morning workouts at Churchill Downs. Omaha Beach was scratched from the Derby due to a throat condition. April 23, 2019. By Pat McDonogh, Courier Journal

Trainer Bob Baffert walks to the track with two of his horses, Flor De La Mar and Game Winner. Flor De La Mar will compete in the Kentucky Oaks. Game Winner is the favorite for the Kentucky Derby. May 2, 2019. By Pat McDonogh, Courier Journal

Trainer Bob Baffert ponders a question outside his barn on the backside of Churchill Downs. Baffert has three horses in the Kentucky Derby, Improbable, Roadster and Game Winner. May 2, 2019. By Pat McDonogh, Courier Journal

Trainer Todd Pletcher talks to the media about his Kentucky Derby horses, Spinoff and Cutting Humor, Wednesday morning after training. "Both horses give me the indication they'll get the distance as well. From a training perspective, we've seen them do things in the morning that are consistent with the horses that we've brought here that have done very well. We like them both a lot. We'll just see." May 1, 2019 Matt Stone/Courier Journal

The wind blows Flor de la Mar's mane while being bathed at Churchill Downs. The Bob Baffert gained filly was 2nd in the Santa Anita Oaks and is scheduled to run in the Kentucky Oaks. April 28, 2019 By Pat McDonogh, Courier Journal

Trainer Mark Casse watched his horses train in the morning at Churchill Downs. Casse has entered War of Will in the Kentucky Derby and Chocolate Kisses in the Kentucky Oaks. April 30, 2019 By Pat McDonogh, Courier Journal

Koichi Tsunoda watched from the sidelines as the media surrounded his stable to get the first look at Master Fencer, who traveled from Japan to compete in the Kentucky Derby, April 30, 2019. By Pat McDonogh, Courier Journal

Jimmy Barnes, assistant trainer in the Bob Baffert stables, looks out from the barn where Kentucky Derby hopefuls Game Winner, Improbable and Roadster are housed. April 29, 2019 By Pat McDonogh, Courier Journal

Fornatale, an author who has tackled a range of topics, got to know Maloney years ago and bugged him for more than a decade to write the book and tell his stories.

Finally, Maloney agreed to do it.

“There’s a lot of secrecy that surrounds a lot of professional gamblers,” Fornatale said, “and even Mike was very guarded for a long time. But it just came at the right time in his career to put the book out there in the world, and I’m very glad that he chose to do that.”

Maloney wrote the book as a way to honor his late father, who taught him the game. Bud Maloney was Mike’s sidekick for years before dying in 2017, having read a draft of his son’s book, a mixture of personal anecdotes with detailed wagering advice.

Bud’s presence remains large in Mike’s workspace. Framed on the wall of his office is a lighthearted lifetime honorary degree bestowed by Bud to Mike and a small number of others deemed worthy.

“By the power vested in me by the State of Insanity,” it reads, “and by the years of hard knocks, near misses, might have beens, should have beens, almost misses, ifs, ands, buts, and bruises, I hearby proclaim the holder of this certificate to be a Equine Performance Analyst. … The above being superior to a mere handicapper in overall knowledge, expertise and money almost won.”

“I feel like my game is as good now if not better than it’s ever been,” he said. “That encourages me that I have time left. My biggest concerns are not with how long I want to work. I enjoy working. Even though it sounds like an awful grind … if you’re doing what you love, it’s not nearly as bad as doing something else these kind of hours.”

“I think it’s to the point in his life where people know about him and he doesn’t want to disappoint,” Bowie, the former UK player, said. “He’s probably fearful of not performing. … All I know is this: I know what line I’m getting in. It’s going to be Mike’s line. I’m sure there’s others out there that have spent lifetimes preparing themselves and knowing what handicapping is about, but this guy is for real.”